Sodium Methoxide → HCID 67266237, compound

HRID 1990837Notes

Reaction equation

HRID 1990837 reaction equation
Cl[C:2]1[C:7]([O:8][CH2:9][CH3:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:11][O-:12].[Na+]>O>[CH2:9]([O:8][C:7]1[C:2]([O:12][CH3:11])=[N:3][CH:4]=[CH:5][CH:6]=1)[CH3:10]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 122934752-chloro-3-ethoxypyridine

Product 1

HCID 67266237HCID 67266237, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-chloro-3-ethoxy-pyridine (3.0 g, 19.0 mmol, 1.0 equiv) and sodium methoxide (8.8 mL, 47.5 mmol, 2.5 equiv, 5.4 M solution in methanol) was heated to 100° C. under microwave irradiation for 20 min. The crude reaction mixture was poured into water (100 mL) and extracted with dichloromethane (3×100 mL). The combined organic phases were dried over MgSO4 and the solvent removed by evaporation under reduced pressure to yield 2.75 g (95%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.40 (t, J=7.0 Hz, 3H), 3.94 (s, 3H), 4.02 (q, J=7.0 Hz, 2H), 6.75 (dd, J=7.8 Hz, J=5.0 Hz, 1H), 6.96 (dd, J=7.8 Hz, J=1.5 Hz, 1H), 7.65 (dd, J=5.0 Hz, 1=1.5 Hz, 1H). 13C NMR (75 MHz, CDCl3): δ 13.62, 52.53, 63.25, 115.69, 117.53, 136.13, 142.45, 153.84. MS (ISP): 153.8 [M+H]+.

Workup

  1. customThe crude reaction mixture
  2. extractionextracted with dichloromethane (3×100 mL)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe solvent removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-d19417946e9d4a4e943ceb95fa9f445e
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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